The Chesterton Challenge Half Marathon Run and 5K Run/Walk takes place October 11, 2026, in Chestertown, Maryland, at Wilmer Park. The event offers a 1-mile option and a half-marathon distance, accommodating both walkers and runners. The race starts at 9:00 AM. Entry fees range from $25 to $60 depending on the distance selected. If you're traveling for this fall race, you'll want accommodation within easy reach of Wilmer Park for a straightforward morning commute before the early start time.
From the Race Organizer
Benefits: Kent Association of Riding Therapy, Inc. (KART) Registration opens at 8 a.m. - Half Marathon Run & 5K Run/Walk start at 9 a.m. Registration: Race day registration will be available! Packet pickup starts at 8 a.m. and races start at 9 a.m. at Wilmer Park, Chestertown, Maryland. Silent Hero Donation: Can't make this event but would like to show your support? Register as a Silent Hero! Food for Purchase will be available! Benefactor: Kent Association of Riding Therapy (KART) was founded in 1984 to help children and adults with disabilities enhance their social and developmental growth. KART uses a multi-faceted program involving therapeutic horseback riding, barn management, and caring for the horse. Packet Pickup: All race packets can be picked up on Sunday morning starting at 8 a.m. Race day registration will also be accepted at this time. Directions: Wilmer Park is located across the street from address 400 South Cross Street, Chestertown, MD. For directions, use your GPS or MapQuest. Awards: Unique awards for overall male and female winners in the Half Marathon and 5K Run. Awards presented to the top 2 in 10-year age groups in the Half Marathon and 5K Run. Awards to top 2 male and female finishers in the 5K walk. 5K awards will be presented after the last participant finishes. Half Marathon awards will be presented 3 hours after start. Course: The event starts and finishes at Wilmer Park. The course has gentle rolling terrain and is run entirely on paved country roads. Course Records: Half Marathon: Male - Hasan Butler - 1:21:27 - 2014, Female – Meredith Tulio - 1:28:29 - 2018. 5K Run: Male - Jesse Goodyear - 17:50 - 2015, Female – Lisa Victorius - 20:50 - 2017 Amenities: Quality “Chestertown Challenge Half Marathon & 5K Run/Walk” Tech Shirts guaranteed to all participants registered by Monday, September 30th. Food and refreshments at the finish line! Police controlled roads, mile markers and directional arrows on road. Water stops: Water stops will be located at approximately every two miles on the Half Marathon course, at the turnaround of the 5K, and at the start/finish. Restrooms: Restrooms will be available at the start/finish and on the Half Marathon course. Spectators: While you're waiting for your friends or family members to complete the race, enjoy the beautiful historic Chestertown sites on the Chester River. Visit www.kentcounty.com/tourism. Hotels/Motels/Bed & Breakfast: Visit the following websites for a complete list of hotels/motels and bed & breakfast in the Chestertown and Rock Hall area., www.kentcounty.com/lodging/rockhall_lodging.php Inns & Bed and Breakfast in Chestertown, Maryland Red Roof Inn & Suites Chestertown - ReservationDesk.com Comfort Inn & Suites Chestertown - ReservationDesk.com
Hotels Near This Race
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Chestertown Challenge Half Marathon Run and 5K Run/Walk 2026 — Chestertown, MD
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Race Travel Insurance
Don't forget travel insurance for October 11.
You've trained for months and booked a trip to Chestertown, MD.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is Chestertown Challenge Half Marathon Run and 5K Run/Walk 2026 — Chestertown, MD?
Chestertown Challenge Half Marathon Run and 5K Run/Walk 2026 — Chestertown, MD takes place on October 11, 2026. The race is held in Chestertown, Maryland.
Where is Chestertown Challenge Half Marathon Run and 5K Run/Walk 2026 — Chestertown, MD held?
Chestertown Challenge Half Marathon Run and 5K Run/Walk 2026 — Chestertown, MD is held at Wilmer Park in Chestertown, Maryland.
Where can I find hotels near Chestertown Challenge Half Marathon Run and 5K Run/Walk 2026 — Chestertown, MD?
RaceHotelFinder shows hotels sorted by distance from the race venue in Chestertown. Use the map or list view on this page to compare options and book race weekend accommodation.
